208 PRACTICAL ORGANIC CHEMISTRY
The ether extract is then dried over potassium carbonate and
the ether removed by distillation on the water-bath. The
phenyl methyl carbinol which remains is distilled under reduced
pressure; b. p. 100° at 15 mm. ; IIO~IIIQ at 28 mm. ; 118° at
40 mm. Yield, 20 grams.
The same method may be used without modification for pre-
paring phenyl ethyl carbinol using a corresponding quantity of
ethyl iodide. See Appendix^ p. 307.
Benzoyl Chloride, C0H5CO.C1
Wohler, AnnaJen, 1832, 3, 262 ; Cahours, Annalcn, 1846, 60,
28 grms. benzoic acid.
50 „ phosphorous pentachloride.
A round flask (250 c.c.) is fitted with an air-condenser. The
phosphorous pentachloride is introduced from the bottle and
weighed by difference. The operation must be conducted in
the fume-cupboard. The benzoic acid is then added, and the
air-condenser attached to the flask.* The action begins almost
immediately, and clouds of hydrochloric fumes are evolved.
The whole contents become liquid and consist of benzoyl
chloride (b. p. 200°), phosphorous oxychloride (b. p. 107°), and
unchanged pentachloride. Most of the oxychloride may be
removed by distilling in vacua on the water-bath. The re-
mainder is fractionated at the ordinary pressure and collected at
190-200°. Yield, 20 —25 grams.
Properties. — Colourless liquid, which fumes in the air and
possesses a pungent smell ; b. p. 198*5° ; sp. gr. 1*214 at 19°.
Reactions. — i. Add a few drops of benzoyl chloride to i c.c. of
water ; the benzoyl chloride does not decompose at once, and
requires warming for some time before it is completely dissolved
(compare acetyl chloride, p. 74).
2. Add 2 c.c. ethyl alcohol to i c.c. benzoyl chloride and
caustic soda solution until alkaline, and warm gently. After a
time the smell of benzoyl chloride disappears, and ethyl benzoate